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Southold: Vacation Rentals (496)

  • 1 - 50 of 496
Additional fees apply. Taxes may be added.
    • 3 BR
    • 2 BA
    • 1 HF BA
    • Sleeps 6
    1 Review
      • 2 BR
      • 1 BA
      • Sleeps 4
      9
        • 3 BR
        • 2 BA
        • Sleeps 8
        10
          • 3 BR
          • 3 BA
          • 1 HF BA
          • Sleeps 8
          4
            • 3 BR
            • 2 BA
            • Sleeps 8
            19
              • 3 BR
              • 2 BA
              • Sleeps 6
              3
                • 6 BR
                • 4 BA
                • Sleeps 14
                1 Review
                  • 4 BR
                  • 3 BA
                  • Sleeps 14
                  2 Reviews
                    • 3 BR
                    • 2 BA
                    • Sleeps 8
                    2 Reviews
                      • 5 BR
                      • 2 BA
                      • Sleeps 10
                      10
                        • 2 BR
                        • 2 BA
                        • Sleeps 5
                        2 Reviews
                          • 2 BR
                          • 1 BA
                          • Sleeps 6
                            • 4 BR
                            • 2 BA
                            • Sleeps 9
                            1 Review
                              • 4 BR
                              • 3 BA
                              • Sleeps 10
                              27
                                • 2 BR
                                • 1 BA
                                • 1 HF BA
                                • Sleeps 5
                                6
                                  • 4 BR
                                  • 2 BA
                                  • Sleeps 10
                                  6
                                    • 1 BR
                                    • 1 BA
                                    • Sleeps 3
                                    7
                                      • 3 BR
                                      • 2 BA
                                      • Sleeps 7
                                      1 Review
                                        • 3 BR
                                        • 2 BA
                                        • Sleeps 5
                                        1 Review
                                          • 4 BR
                                          • 2 BA
                                          • Sleeps 11
                                          13
                                            • 3 BR
                                            • 2 BA
                                            • Sleeps 8
                                            6
                                              • 4 BR
                                              • 3 BA
                                              • 1 HF BA
                                              • Sleeps 10
                                              2 Reviews
                                                • 3 BR
                                                • 3 BA
                                                • Sleeps 8
                                                  • 4 BR
                                                  • 4 BA
                                                  • Sleeps 10
                                                    • 2 BR
                                                    • 1 BA
                                                    • Sleeps 6
                                                    10
                                                      • 2 BR
                                                      • 1 BA
                                                      • Sleeps 4
                                                      6
                                                        • 2 BR
                                                        • 1 BA
                                                        • 1 HF BA
                                                        • Sleeps 6
                                                        50
                                                          • 2 BR
                                                          • 1 BA
                                                          • Sleeps 4
                                                          13
                                                            • 4 BR
                                                            • 2 BA
                                                            • Sleeps 8
                                                              • 3 BR
                                                              • 1 BA
                                                              • 1 HF BA
                                                              • Sleeps 6
                                                              1 Review
                                                                • 2 BR
                                                                • 1 BA
                                                                • Sleeps 4
                                                                  • 3 BR
                                                                  • 2 BA
                                                                  • Sleeps 6
                                                                    • 3 BR
                                                                    • 2 BA
                                                                    • Sleeps 6
                                                                    7
                                                                      • 3 BR
                                                                      • 2 BA
                                                                      • Sleeps 6
                                                                      4
                                                                        • 4 BR
                                                                        • 3 BA
                                                                        • Sleeps 6
                                                                        3
                                                                          • 4 BR
                                                                          • 2 BA
                                                                          • Sleeps 10
                                                                          6
                                                                            • 5 BR
                                                                            • 4 BA
                                                                            • 1 HF BA
                                                                            • Sleeps 10
                                                                            5
                                                                              • 5 BR
                                                                              • 3 BA
                                                                              • Sleeps 12
                                                                                • 5 BR
                                                                                • 4 BA
                                                                                • Sleeps 10
                                                                                10
                                                                                  • 3 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 6
                                                                                    • 3 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 6
                                                                                    2 Reviews
                                                                                      • 2 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 6
                                                                                      3
                                                                                        • 5 BR
                                                                                        • 3 BA
                                                                                        • Sleeps 7
                                                                                          NEW!
                                                                                          • 3 BR
                                                                                          • 3 BA
                                                                                          • Sleeps 6
                                                                                          1 Review
                                                                                            • 3 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 5
                                                                                              • 3 BR
                                                                                              • 2 BA
                                                                                              • 1 HF BA
                                                                                              • Sleeps 8
                                                                                                • 3 BR
                                                                                                • 1 BA
                                                                                                • 1 HF BA
                                                                                                • Sleeps 6
                                                                                                4
                                                                                                  • 3 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 6
                                                                                                  5
                                                                                                    NEW!
                                                                                                    • 4 BR
                                                                                                    • 3 BA
                                                                                                    • Sleeps 10
                                                                                                      • 3 BR
                                                                                                      • 3 BA
                                                                                                      • 1 HF BA
                                                                                                      • Sleeps 8
                                                                                                      • 1 - 50 of 496
                                                                                                       

                                                                                                      Recent Southold Reviews

                                                                                                      Peaceful Bliss, best sunsets in the world!

                                                                                                      5 of 5
                                                                                                      This sound front property is one of the most unique places ive ever stayed in. I've seen sunsets in Santorini, Rome, and Barcelona, and the sunsets available to you from the beach side deck of this house can go round for round with any of the former mentioned. Everything was clean and the layout and amenities were everything and more that we asked for on our stay. Marilyn shared with us some of the local secrets of best restaurants to go to as well as what areas on the inlet provided the best kayaking. My girlfriend and I live in Boston, and this short trip over the New London ferry only took us 3 hours door to door! We went to Noah's, and industry Standard in Green Port village, as well as ventured over to Love Lane Kitchen in Mattituck, all were highly recommended by Marilyn, and none of them let down. We went to a few wineries as well, Costello di borghese had some of the best Pinot Noir that I have ever had, and sparkling pointe provided some great outdoor scenery with some crisp blanc de blancs to keep you cool. We liked both wines so much we couldn't leave without picking up a few bottles. Overall it was an amazing experience, the time flew by unfortunately too fast, and I cant wait to get back to my Long Island paradise!
                                                                                                      • Submitted: Sep 7, 2016
                                                                                                      • Stayed: Jul 2016

                                                                                                      Beautiful Soundview home

                                                                                                      5 of 5
                                                                                                      We had a wonderful and relaxing time at this beautiful home. Large kitchen with all the amenities one could want. Short walk to the beach. The water in the long Island sound was warm and just right for swimming and just relaxing. Southold is quaint with plenty of good restaurants and shops. The owner is very attentive and resolved a very minor issue in a manner of minutes. Looking forward to returning again for our family vacation.
                                                                                                      • Submitted: Sep 7, 2016
                                                                                                      • Stayed: Aug 2016

                                                                                                      Fabulous vacation home for North Fork getaway!

                                                                                                      5 of 5
                                                                                                      We truly enjoyed staying at this gorgeous home for our family vacation on the North Fork. It's situated on a great piece of property on the water with easy access for kayaking, fishing and swimming. The house is beautifully decorated, updated, extremely clean, and has everything you need for a relaxing getaway. The kayaks and ping pong table were a big hit. We loved exploring the waterways and trying to catch fish. The back deck has a great view and is perfect for a morning cup of coffee or dining outside. It's a quick drive to Southold, the wineries and Greenport, with lots of restaurants, shops and things to do with the family. Plus the owners, John and Lorena, are super warm and welcoming. We'd definitely recommend this vacation home to our family and friends!
                                                                                                      • Submitted: Sep 6, 2016
                                                                                                      • Stayed: Aug 2016